This invention relates to a novel derivative of 11-aza-10-deoxo-10-dihydroerythromycin A useful as an antibacterial agent, to intermediates therefor, and to processes for their preparation. More particularly it relates to the N-methyl derivative of 11-aza-10-deoxo-10-dihydroerythromycin A, to pharmaceutically acceptable acid addition salts thereof, and to certain alkanoyl derivatives thereof useful as antibacterial agents, to intermediates therefor, and to processes for their preparation.
Erythromycin A is a macrolide antibiotic produced by fermentation and described in U.S. Pat. No. 2,653,899. Numerous derivatives of erythromycin A have been prepared in efforts to modify its biological and/or pharmacodynamic properties. Erythromycin A esters with mono- and dicarboxylic acids are reported in Antibiotics Annual, 1953-1954, Proc. Symposium Antibiotics (Washington, D.C.), pages 500-513 and 514-521, respectively. U.S. Pat. No. 3,417,077 describes the cyclic carbonate ester of erythromycin A, the reaction product of erythromycin A and ethylene carbonate, as an active and antibacterial agent.
U.S. Pat. No. 4,328,334, issued May 4, 1982, describes 11-aza-10-deoxo-10-dihydroerythromycin A, certain N-acyl- and N-(4-substituted benzenesulfonyl) derivatives thereof having antibacterial properties, and a process for their preparation.
The alkylation of primary and/or secondary amine groups of compounds which include a tertiary amine group is generally complicated. However, it is common practice to protect tertiary amine groups in such compounds by converting them to N-oxides prior to alkylation (Greene, "Protective Groups in Organic Synthesis", John Wiley & Sons, Inc., N.Y., 1981, pg. 281).